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AITA for dating my one night stand’s dad?

by Charlie Brown
March 15, 2026
in Aita
Reading Time: 4 mins read
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From the moment she stepped into the office, it was clear that Jack’s infatuation with her was a silent storm brewing beneath the surface. What began as persistent insistence slowly morphed into a short-lived, hollow encounter that left her feeling used and dismissed. Yet, even as she distanced herself from Jack’s childish grasp, the shadows of his obsession lingered, casting an uncomfortable tension over every interaction.

Then, unexpectedly, she found solace and passion in the arms of Peter, her boss and Jack’s father—a man whose presence was a stark contrast to the boy who once chased her. Their connection was electric, grounded in respect and desire, shaking the foundations of their tangled family ties. But love, in this twisted triangle, only ignited deeper wounds, as Jack’s fury erupted, threatening to unravel everything she had fought so hard to build.

AITA for dating my one night stand’s dad?

I(F24) started my job 2 years ago. From the first...

He literally begged me to date him and after months...

It lasted a short amount of time and he seemed...

A few months ago I started dating my boss Peter...

He has everything I want in a man. He is...

He called me a bunch of names and demanded we...

Does he seriously believe that he can demand that we...

According to organizational psychologist Dr. Kegan Chavis, “Workplace relationships, especially those involving hierarchical differences or immediate family connections, create complex webs of power and loyalty that often supersede personal feelings and require meticulous navigation to prevent organizational disruption.”

The core issue here involves boundary violations and an imbalance of power, even if the immediate relationship is between peers (the poster and Peter). The poster’s initial dating of Jack, followed by ending things only to immediately pursue his father, creates a predictable, high-conflict scenario. Jack’s reaction, while immature in his demands, stems from feelings of rejection and betrayal within his family structure. The poster appears to minimize the emotional impact on Jack, focusing solely on her own satisfaction with Peter, which demonstrates a lack of consideration for the emotional labor required to manage this unique family dynamic.

While the poster and Peter are adults, the proximity of this relationship to the workplace adds layers of ethical complexity. The poster’s actions were appropriate in pursuing a relationship she desires, but her execution—especially given the existing connection to Jack—was socially and professionally risky. A more constructive approach would have involved a private, firm conversation with Jack, validating his feelings while clearly stating that the decision to date Peter is final and non-negotiable, perhaps even suggesting a brief period of professional distance if the tension severely impacts work output.

What do you think of this story?





AFTER THIS STORY DROPPED, REDDIT WENT INTO MELTDOWN MODE – CHECK OUT WHAT PEOPLE SAID.

Dearm000n This is just gross. Your both a*sholes and I...

FA-TH-UR lol!!! Girl it sounds like you're only with Jack...

The fact that this grown man has no problem dating...

What a family to be entering into please keep us...

sinnerprince1 YTA jack's stepmom

Dapper_Internet_8576 Thats both pathetic and disgusting

 Both you and your boss are assholes

Giovanny_diaz_ YTA. Dating someone's parent after a bad fling with...

mosstalgia YTA, however you are not as bad as this...

If you marry this man, be aware that the fruit...

Fuzzy-Bike-8813 Who's next his grandfather?

The original poster is facing significant tension after choosing to date her boss, Peter, despite his son Jack’s prior romantic interest and subsequent angry reaction. She feels justified in her relationship with Peter due to their compatibility and mutual attraction, viewing Jack’s demands for them to separate as unreasonable and entitled.

Given the intense family conflict arising from this age-gap relationship between an employee and her boss, should the priority be maintaining professional harmony and familial peace, or does the poster have an absolute right to pursue happiness in her private life, regardless of the consequences for workplace or family dynamics?

Charlie Brown

Charlie is a creative mind who enjoys writing about art, music, and culture.

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